Process for preparing certain 1,3,4-dioxazol-2-ones and products

Abstract

Cyclic nitrile carbonate group-containing chloroformate of the general formula: ##EQU1## is condensed with polyfunctional nucleophilic compound of the general formula: HT-Y TH].sub.x , wherein R is an aliphatic hydrocarbon, T is O, S or NR', wherein R' is hydrogen or an essentially hydrocarbonaceous group, Y consists essentially of carbon and hydrogen, and x is 1 to 3, to yield hydrogen chloride as the elimination product and cyclic nitrile carbonate group-containing condensate of the general formula: ##EQU2## AS THE ADDITION PRODUCT. The addition product is useful as, inter alia, a precursor for a carbonate, urethane or thiocarbonate group-containing polyurethane, polyurea, or polythiourethane, these polymers being in turn useful in coating, molding, adhesive, and the like compositions.

We claim: 
     
       1. A cyclic nitrile carbonate group-containing compound of the formula: wherein R is aliphatic hydrocarbon of 2 to 11 carbon atoms, at least 2 carbon atoms of which separate the non-ring oxygen atom from the nitrile carbon atom, Y is an essentially hydrocarbonaceous organic radical free of groups that would be reactive with the nitrile carbonate groups and has a molecular weight of up to about 9,900, x is 1 to 3 and T is O, S, NR' or ##EQU22## R' being hydrogen or an essentially hydrocarbonaceous organic radical free of groups that would be reactive with the cyclic nitrile carbonate groups having up to 10 carbon atoms, which radical is either monovalent and bonded only to the nitrogen atom of T, or is divalent and either (a) bonded to Y as well as to the nitrogen atom of T or (b) bonded to another nitrogen atom of another T as well as to said first nitrogen atom of said first T.   
     
     
       2. The compound of claim 1 wherein R has at least 3 carbon atoms and at least 3 carbon atoms thereof separate the non-ring oxygen atom from the nitrile carbon atom. 
     
     
       3. The compound of claim 2 wherein R is pentamethylene. 
     
     
       4. The compound of claim 2 wherein Y is tetramethylene and T is O or NH. 
     
     
       5. The compound of claim 2 wherein Y is hexamethylene and T is O or NH. 
     
     
       6. The compound of claim 2 wherein Y is dimethylene and T is S or NH. 
     
     
       7. The compound of claim 2 wherein Y is --CH 2  --CH 2  --S--CH 2  --CH 2  -- and T is S. 
     
     
       8. The compound of claim 2 wherein Y is ##SPC3## and T is O.   
     
     
       9. The compound of claim 2 wherein Y is ##SPC4## and T is O.   
     
     
       10. The compound of claim 1 wherein x is 1 and T--Y--T is 3 amino piperidine. 
     
     
       11. The compound of claim 1 wherein x is 1 and T--Y--T is piperazine.